Highly enantioselective epoxidation of styrenes: Implication of an electronic effect on the competition between spiro and planar transition states

Proceedings of the National Academy of Sciences of the United States of America

Volumn 101, Issue 16, 2004, Pages 5794-5798

  Hickey, Matthew ^a   Goeddel, David ^a   Crane, Zackary ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBOXYLIC ACID DERIVATIVE; KETONE; OXAZOLIDINONE DERIVATIVE; STYRENE;

ARTICLE; CATALYST; ELECTRONICS; ENANTIOMER; ENANTIOSELECTIVITY; EPOXIDATION; MOLECULAR INTERACTION; PRIORITY JOURNAL;

EPOXY COMPOUNDS; KETONES; MODELS, MOLECULAR; STEREOISOMERISM; STYRENES;

EID: 1942501759     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0307548101     Document Type: Article

References (109)

1. Johnson, R. A. & Sharpless, K. B. (1993) in Catalytic Asymmetric Synthesis, ed. Ojima, I. (VCH, New York), pp. 103-158.
2. Katsuki, T. & Martin, V. S. (1996) Org. React. 48, 1-299.
3. Johnson, R. A. & Sharpless, K. B. (2000) in Catalytic Asymmetric Synthesis, ed. Ojima, I. (VCH, New York), pp. 231-280.
4. Jacobsen, E. N. (1993) in Catalytic Asymmetric Synthesis, ed. Ojima, I. (VCH, New York), pp. 159-202.
5. Collman, J. P., Zhang, X., Lee, V. J., Uffelman, E. S. & Brauman, J. I. (1993) Science 261, 1404-1411.
6. Mukaiyama, T. (1996) Aldrichim. Acta 29, 59-76.
7. Katsuki, T. (2000) in Catalytic Asymmetric Synthesis, ed. Ojima, I. (VCH, New York), pp. 287-325.
8. Porter, M. J. & Skidmore, J. (2000) Chem. Commun., 1215-1225.
9. Lauret, C. & Roberts, S. M. (2002) Aldrichim. Acta 35, 47-51.
10. Nemoto, T., Ohshima, T. & Shibasaki, M. (2002) J. Synth. Org. Chem. Jpn. 60, 94-105.
11. Corey, E. J., Shibata, S. & Bakshi, R. K. (1988) J. Org. Chem. 53, 2861-2863.
12. Hamada, T., Torii, T., Izawa, K., Noyori, R. & Ikariya, T. (2002) Org. Lett. 4, 4373-4376.
13. Kolb, H. C. & Sharpless, K. B. (1992) Tetrahedron 48, 10515-10530.
14. Weissman, S. A., Rossen, K. & Reider, P. J. (2001) Org. Lett. 3, 2513-2515.
15. Tokunaga, M., Larrow, J. F., Kakiuchi, F. & Jacobsen, E. N. (1997) Science 277, 936-938.
16. Groves, J. T. & Myers, R. S. (1983) J. Am. Chem. Soc. 105, 5791-5796.
17. Mansuy, D., Battioni, P., Renaud, J.-P. & Guerin, P. (1985) J. Chem. Soc. Chem. Commun., 155-156.
18. O'Malley, S. & Kodadek, T. (1989) J. Am. Chem. Soc. 111, 9116-9117.
19. Groves, J. T. & Viski, P. (1990) J. Org. Chem. 55, 3628-3634.
20. Halterman, R. L. & Jan, S.-T. (1991) J. Org. Chem. 56, 5253-5254.
21. Naruta, Y., Tani, F., Ishihara, N. & Maruyama, K. (1991) J. Am. Chem. Soc. 113, 6865-6872.
22. Konishi, K., Oda, K.-I., Nishida, K., Aida, T. & Inoue, S. (1992) J. Am. Chem. Soc. 114, 1313-1317.
23. Naruta, Y., Ishihara, N., Tani, F. & Maruyama, K. (1993) Bull. Chem. Soc. Jpn. 66, 158-166.
24. Collman, J. P., Lee, V. J., Zhang, X., Ibers, J. A. & Brauman, J. I. (1993) J. Am. Chem. Soc. 115, 3834-3835.
25. Collman, J. P., Lee, V. J., Kellen-Yuen, C. J., Zhang, X., Ibers, J. A. & Brauman, J. I. (1995) J. Am. Chem. Soc. 117, 692-703.
26. Berkessel, A. & Frauenkron, M. (1997) J. Chem. Soc. Perkin Trans. 1, 2265-2266.
27. Gross, Z. & Ini, S. (1997) J. Org. Chem. 62, 5514-5523.
28. Lai, T.-S., Zhang, R., Cheung, K.-K., Kwong, H.-L. & Che, C.-M. (1998) Chem. Commun., 1583-1584.
29. Collman, J. P., Wang, Z., Straumanis, A., Quelquejeu, M. & Rose, E. (1999) J. Am. Chem. Soc. 121, 460-461.
30. Zhang, R., Yu, W.-Y., Lai, T.-S. & Che, C.-M. (1999) Chem. Commun., 409-410.
31. Gross, Z. & Ini, S. (1999) Org. Lett. 1, 2077-2080.
32. Reginato, G., Bari, L. D., Salvadori, P. & Guilard, R. (2000) Eur. J. Org. Chem., 1165-1171.
33. Zhang, R., Yu, W.-Y., Wong, K.-Y. & Che, C.-M. (2001) J. Org. Chem. 66, 8145-8153.
34. Zhang, R., Yu, W.-Y., Sun, H.-Z., Liu, W.-S. & Che, C.-M. (2002) Chem. Eur. J. 8, 2495-2507.
35. Zhang, W., Loebach, J. L., Wilson, S. R. & Jacobsen, E. N. (1990) J. Am. Chem. Soc. 112, 2801-2803.
36. O'Connor, K. J., Wey, S.-J. & Burrows, C. J. (1992) Tetrahedron Lett. 33, 1001-1004.
37. Palucki, M., Pospisil, P. J., Zhang, W. & Jacobsen, E. N. (1994) J. Am. Chem. Soc. 116, 9333-9334.
38. Palucki, M., McCormick, G.-J. & Jacobsen, E. N. (1995) Tetrahedron Lett. 36, 5457-5460.
39. Hashihayata, T., Ito, Y. & Katsuki, T. (1997) Tetrahedron 53, 9541-9552.
40. Takeda, T., Irie, R., Shinoda, Y. & Katsuki, T. (1999) Synlett, 1157-1159.
41. Kim, G.-J. & Shin, J.-H. (1999) Tetrahedron Lett. 40, 6827-6830.
42. Nakata, K., Takeda, T., Mihara, J., Hamada, T., Irie, R. & Katsuki, T. (2001) Chem. Eur. J. 7, 3776-3782.
43. Davis, F. A., Harakal, M. E. & Awad, S. B. (1983) J. Am. Chem. Soc. 105, 3123-3126.
44. Davis, F. A. & Chattopadhyay, S. (1986) Tetrahedron Lett. 27, 5079-5082.
45. Aggarwal, V. K. & Wang, M. F. (1996) Chem. Commun., 191-192.
46. Bohe, L., Lusinchi, M. & Lusinchi, X. (1999) Tetrahedron 55, 141-154.
47. Takahashi, O., Umezawa, J., Furuhashi, K. & Takagi, M. (1989) Tetrahedron Lett. 30, 1583-1584.
48. Allain, E. J., Hager, L. P., Deng, L. & Jacobsen, E. N. (1993) J. Am. Chem. Soc. 115, 4415-4416.
49. Zaks, A. & Dodds, D. R. (1995) J. Am. Chem. Soc. 117, 10419-10424.
50. Lakner, F. J., Cain, K. P. & Hager, L. P. (1997) J. Am. Chem. Soc. 119, 443-444.
51. Hollmann, F., Lin, P.-C., Witholt, B. & Schmid, A. (2003) J. Am. Chem. Soc. 125, 8209-8217.
52. Murray, R. W. (1989) Chem. Rev. (Washington, D.C.) 89, 1187-1201.
53. Adam, W., Curci, R. & Edwards, J. O. (1989) Acc. Chem. Res. 22, 205-211.
54. Curci, R., Dinoi, A. & Rubino, M. F. (1995) Pure Appl. Chem. 67, 811-822.
55. Denmark, S. E. & Wu, Z. (1999) Synlett, 847-859.
56. Frohn, M. & Shi, Y. (2000) Synthesis (Mass), 1979-2000.
57. Curci, R., Fiorentino, M. & Serio, M. R. (1984) J. Chem. Soc. Chem. Commun., 155-156.
58. Curci, R., D'Accolti, L., Fiorentino, M. & Rosa, A. (1995) Tetrahedron Lett. 36, 5831-5834.
59. Denmark, S. E., Forbes, D. C., Hays, D. S., DePue, J. S. & Wilde, R. G. (1995) J. Org. Chem. 60, 1391-1407.
60. Brown, D. S., Marples, B. A., Smith, P. & Walton, L. (1995) Tetrahedron 51, 3587-3606.
61. Yang, D., Yip, Y.-C., Tang, M.-W., Wong, M.-K., Zheng, J.-H. & Cheung, K.-K. (1996) J. Am. Chem. Soc. 118, 491-492.
62. Yang, D., Wang, X.-C., Wong, M.-K., Yip, Y.-C. & Tang, M.-W. (1996) J. Am. Chem. Soc. 118, 11311-11312.
63. Song, C. E., Kim, Y. H., Lee, K. C., Lee, S. G. & Jin, B. W. (1997) Tetrahedron Asymmetry 8, 2921-2926.
64. Adam, W. & Zhao, C.-G. (1997) Tetrahedron Asymmetry 8, 3995-3998.
65. Denmark, S. E., Wu, Z., Crudden, C. M. & Matsuhashi, H. (1997) J. Org. Chem. 62, 8288-8289.
66. Wang, Z.-X. & Shi, Y. (1997) J. Org. Chem. 62, 8622-8623.
67. Adam, W., Fell, R. T., Saha-Moller, C. R. & Zhao, C.-G. (1998) Tetrahedron Asymmetry 9, 397-401.
68. Armstrong, A. & Hayter, B. R. (1998) Chem. Commun., 621-622.
69. Yang, D., Wong, M.-K., Yip, Y.-C., Wang, X.-C., Tang, M.-W., Zheng, J.-H. & Cheung, K.-K. (1998) J. Am. Chem. Soc. 120, 5943-5952.
70. Yang, D., Yip, Y.-C., Chen, J. & Cheung, K.-K. (1998) J. Am. Chem. Soc. 120, 7659-7660.
71. Adam, W., Saha-Moller, C. R. & Zhao, C.-G. (1999) Tetrahedron Asymmetry 10, 2749-2755.
72. Carnell, A. J., Johnstone, R. A. W., Parsy, C. C. & Sanderson, W. R. (1999) Tetrahedron Lett. 40, 8029-8032.
73. Armstrong, A. & Hayter, B. R. (1999) Tetrahedron 55, 11119-11126.
74. Armstrong, A., Hayter, B. R., Moss, W. O., Reeves, J. R. & Wailes, J. S. (2000) Tetrahedron Asymmetry 11, 2057-2061.
75. Solladie-Cavallo, A. & Bouerat, L. (2000) Org. Lett. 2, 3531-3534.
76. Bortolini, O., Fogagnolo, M., Fantin, G., Maietti, S. & Medici, A. (2001) Tetrahedron Asymmetry 12, 1113-1115.
77. Seki, M., Furutani, T., Imashiro, R., Kuroda, T., Yamanaka, T., Harada, N., Arakawa, H., Kusama, M. & Hashiyama, T. (2001) Tetrahedron Lett. 42, 8201-8205.
78. Armstrong, A., Moss, W. O. & Reeves, J. R. (2001) Tetrahedron Asymmetry 12, 2779-2781.
79. Matsumoto, K. & Tomioka, K. (2002) Tetrahedron Lett. 43, 631-633.
80. Stearman, C. J. & Behar, V. (2002) Tetrahedron Lett. 43, 1943-1946.
81. Denmark, S. E. & Matsuhashi, H. (2002) J. Org. Chem. 67, 3479-3486.
82. Shing, T. K. M. & Leung, G. Y. C. (2002) Tetrahedron 58, 7545-7552.
83. Bortolini, O., Fantin, G., Fogagnolo, M., Forlani, R., Maietti, S. & Pedrini, P. (2002) J. Org. Chem. 67, 5802-5806.
84. Armstrong, A., Ahmed, G., Dominguez-Fernandez, B., Hayter, B. R. & Wailes, J. S. (2002) J. Org. Chem. 67, 8610-8617.
85. Klein, S. & Roberts, S. M. (2002) J. Chem. Soc. Perkin Trans. 1, 2686-2691.
86. Shing, T. K. M., Leung, Y. C. & Yeung, K. W. (2003) Tetrahedron 59, 2159-2168.
87. Sartori, G., Armstrong, A., Maggi, R., Mazzacani, A., Sartorio, R., Bigi, F. & Dominguez-Fernandez, B. (2003) J. Org. Chem. 68, 3232-3237.
88. Chan, W.-K., Yu, W.-Y., Che, C.-M. & Wong, M.-K. (2003) J. Org. Chem. 68, 6576-6582.
89. Tu, Y., Wang, Z.-X. & Shi, Y. (1996) J. Am. Chem. Soc. 118, 9806-9807.
90. Wang, Z.-X., Tu, Y., Frohn, M., Zhang J.-R. & Shi, Y. (1997) J. Am. Chem. Soc. 119, 11224-11235.
91. Shu, L. & Shi, Y. (2001) Tetrahedron 57, 5213-5218.
92. Tian, H., She, X., Shu, L., Yu, H. & Shi, Y. (2000) J. Am. Chem. Soc. 122, 11551-11552.
93. Tian, H., She, X., Xu, J. & Shi, Y. (2001) Org. Lett. 3, 1929-1931.
94. Tian, H., She, X., Yu, H., Shu, L. & Shi, Y. (2002) J. Org. Chem. 67, 2435-2446.
95. Shu, L., Wang, P., Gan, Y. & Shi, Y. (2003) Org. Lett. 5, 293-296.
96. Archelas, A. & Furstoss, R. (1999) J. Org. Chem. 64, 6112-6114.
97. Doussot, J., Guy, A., Siaugue, J.-M., Ferroud, C. & Guieres, A. F. (1999) Chirality 11, 541-545.
98. Pews, R. G. (1967) J. Am. Chem. Soc. 89, 5605-5608.
99. Pedragosa-Moreau, S., Morisseau, C., Zylber, J., Archelas, A., Baratti, J. & Furstoss, R. (1996) J. Org. Chem. 61, 7402-7407.
100. Moussou, P., Archelas, A., Baratti, J. & Furstoss, R. (1998) J. Org. Chem. 63, 3532-3537.
101. Baumstark, A. L. & McCloskey, C. J. (1987) Tetrahedron Lett. 28, 3311-3314.
102. Baumstark, A. L. & Vasquez, P. C. (1988) J. Org. Chem. 53, 3437-3439.
103. Bach, R. D., Andres, J. L., Owensby, A. L., Schlegel, H. B. & McDouall, J. J. W. (1992) J. Am. Chem. Soc. 114, 7207-7217.
104. Houk, K. N., Liu, J., DeMello, N. C. & Condroski, K. R. (1997) J. Am. Chem. Soc. 119, 10147-10152.
105. Jenson, C., Liu, J., Houk, K. N. & Jorgensen, W. L. (1997) J. Am. Chem. Soc. 119, 12982-12983.
106. Armstrong, A., Washington, I. & Houk, K. N. (2000) J. Am. Chem. Soc. 122, 6297-6298.
107. Deubel, D. V. (2001) J. Org. Chem. 66, 3790-3796.
108. Frohn, M., Dalkiewicz, M., Tu, Y., Wang, Z.-X. & Shi, Y. (1998) J. Org. Chem. 63, 2948-2953.
109. Wang, Z.-X., Cao, G.-A. & Shi, Y. (1999) J. Org. Chem. 64, 7646-7650.